


Jester wins again

by asterCrash



Series: dressed like a daydream [2]
Category: Critical Role (Web Series)
Genre: Aphrodisiacs, Bondage, Dubious Consent, F/F, F/M, Jester has godly powers and is not shy about using them, Non-Consensual Drug Use, Widobrave-Centric
Language: English
Status: Completed
Published: 2020-05-31
Updated: 2020-05-31
Packaged: 2021-03-02 18:40:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,801
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24471448
Author URL: https://archiveofourown.org/users/asterCrash/pseuds/asterCrash
Summary: Jester is a little sick of Caleb pining for dear sweet precious Veth Brenatto and decides to use her powers for good, or something almost like it.Caleb wakes up tied to a chair, and immediately curses himself for not being surprised by that.
Relationships: Jester Lavorre/Nott, Jester Lavorre/Nott/Caleb Widogast, Nott/Caleb Widogast
Series: dressed like a daydream [2]
Series URL: https://archiveofourown.org/series/1767229
Comments: 7
Kudos: 59





	Jester wins again

**Author's Note:**

  * For [Capitola](https://archiveofourown.org/users/Capitola/gifts).



> Written for and inspired by the most wonderful and amazing Capitola <3

Caleb wakes up tied to a chair, and immediately curses himself for not being surprised by that. How little must he think of himself for waking up like this to seem completely reasonable. His shoulders ache, as his arms are bound behind him; careful bonds, but not so careful as to give him a chance to escape. A quick flex confirms his hands are definitely going nowhere fast, cords of softest silk have been woven through his fingers to prevent any magical tricks that might lead to a breakout. He attempts to straighten in the seat but finds his legs bound as well, each to a different leg of the chair, spreading his thighs apart and making it uncomfortably apparent that whoever tied him here took the liberty of undoing his trousers as well. The darkness of the room envelopes him like a blanket, his eyes still adjusting, and the cool night air caresses his manhood. Traitorous organ that it is, it begins to stiffen.

A slight moan coming from the darkness catches his attention, and he focuses until he can make out two silhouettes ahead of him, one medium, one small, the latter sitting upon the first and faintly shifting in place. The head of the medium shape bends down to the neck of the small and there comes a wet sucking noise, quickly covered up by a louder moan than before.

“I don’t suppose you have a light?” He asks the shape in the darkness and it laughs, a purring, familiar laugh.

Jester doesn’t respond in words, but as unearthly lights appears around the room,  _ his _ room he can now see, her smile answers for her.

“Oh, you’re finally awake!” She exclaims. She hasn’t been the same since TravelerCon, her eyes still those shimmering, constantly changing rainbows, like pools of water illuminated from within. She seemed to glow herself, dressed in chaotic silks and velvet, not clothes so much as loose cloth twisted around her.

Veth squirms in her lap, writhing as if to get away from the soft blue hand buried up her skirt, but only driving herself further onto it in the process. Her dress is unbuttoned and her soft brown breasts hang out on display. His eyes can’t avoid the way her nipples stiffened, and he can’t avoid the look she gives him when she catches him staring.

“I’ve been thinking,” Jester begins, as if this is just an ordinary conversation between friends. “That this ‘will they, won’t they’ drama has gotten a little stale.” She looks at something that isn’t there, and shoots it an expression that conveys a secret meaning, something Caleb can only guess. “So I thought I’d help you two along.”

Veth whimpers at her touch and Jester briefly shuffles in place to reposition the halfling on her lap.

“Veth is  _ very _ into you Caleb.” Another whimper, it might be described as a cry. “Ever since she got her body back she can’t seem to keep her hands from wandering, and so very often it’s you she’s thinking of when she does it.” Veth sobs, but doesn’t deny it. Jester’s eyes are luminescent and terrifying to behold. “I’ve seen the fantasies she has of you, Caleb. Would you like to see how dirty they get?”

“Jester, you should stop this,” Caleb starts, but the chaotic rainbow of her eyes tilts down to his erection as if she didn’t even need to point out his hypocrisy. She mercilessly pulls her hand upwards and Veth bucks against her, the sounds she makes causing Caleb’s dick to twitch in place.

“You’re into her too, though you don’t want to admit it. You’re so jealous of her husband you’ve even pictured him tied up, helplessly watching as you claimed his wife for your own.” Jester pauses her sexy villain monologue to bend down and lick the bruises she’d left on Veth’s throat.

“You should stop,” Veth says, speaking at last, even though her hips are still clearly moving. “He doesn’t want this, you don’t have to force him to-”   
“She’s not forcing me,” Caleb says, surprising himself. “I mean, the ropes, ja, but she’s not lying.” A look passes between them, and for a moment they aren’t in whatever kinky fantasy Jester has set up for them, they’re just together, like they always were, curled up in bed, talking until they fell asleep. “I want you,” Caleb clarifies, as if his erection isn’t saying the exact same thing.

Veth looks close to tears, Jester has to hold her back with her other hand, though the one between Veth’s legs never stops moving.

“You should let her go,” Caleb says, summoning all the authority he can with his hands tied behind his back and his dick hanging out. Jester just laughs at him.

“Oh I’m not forcing her to stay. I had her mix up a little aphrodisiac to slip into Yasha’s tea, said it was to help her unwind. A little prank, you know?” Her eyes grow brighter, the colours swirling with a greater fervour than ever. “Swapping the cups was really too easy. I didn’t account for the difference in body weight though.” Veth moans as if on cue, and Caleb sees the way she clenches her thighs now, pushing herself onto Jester’s fingers, holding herself in place. The room is quiet enough that the wet, needy noises coming from between her legs very nearly echo.

“The thing is, she really has been a naughty girl, keeping this crush from you the whole time.” Jester pinches a dark brown nipple between thumb and forefinger and Veth thrashes in place. “So I’ve been taking it slow. She’s only come a few times so far.” Veth seems to curl inwards at that, her whole body shuddering. “Oops, one more.” The waves of her orgasm are clearly hitting, and Jester’s hand changes to slow, languid movements in time with the thrust of Veth’s hips and licks a possessive stripe up her jawline. “You’re not the only one she fantasizes about, after all.”

“Let her go.” Caleb insists. He doesn’t know how to negotiate with whatever Jester is right now, and frankly doesn’t know what he wants either. If his hands were free he could get them both out of here, but the moment he thinks of it, visions come to mind of his hand tight around his manhood, pumping like his life depends on it, Jester and Veth drinking him in with their eyes. The fantasy changes and the word ‘drinking’ becomes so much more literal, their tongues on his cock, his seed spilling into their mouths. Jester exits the fantasy and then it’s just him and Veth, laying her down, being tender as he penetrates her, takes her like her husband does in all his jealous fantasies. He sees himself being rough, but no, that doesn’t suit him, he can’t imagine his hands holding her tightly, beyond perhaps pinning her wrists above her head so he can have all of her exposed to him.

“Do you see?” Jester stage-whispers to Veth, snapping Caleb out of his fantasy as the glow of her eyes recedes just a little and for a moment he could swear he sees blue in there. “Do you see how much he wants you too?”

Veth looks helpless, lost, her eyes search his for answers but then the room shifts colours and he’s looking down at his own body, spread out before her. She checks the taughtness of the ropes holding him out at all angles, arms and legs spread across the carpeted floor like a human sacrifice. She paints his body with warm tinctures and ointments, draws on him with hot wax, tastes his flesh with her tongue and finally takes his manhood in her mouth.

Caleb’s vision swims as he comes back to his body, the imagined taste of his own cock still lingering in his memory.

“Don’t do that, please,” Veth begs, “don’t show him those thoughts.”

Caleb tries to sit up in his chair, leans forward, “ _ Schatz, _ ” he whispers, wanting to tell her it’s alright, he’s here for her, they’re together, but then very suddenly his vision swims again and he’s seeing himself, a dozen versions of himself, all in various positions, all making love to her. He feels the sensation of being penetrated, he tastes her husband and then himself in turn, he feels the electric sensation of his mouth on her breasts and writhes as an orgasm takes her, makes her whole body quake with the sensation until it seems to blot out all thought.

Jester is lazily nibbling at Veth’s ear, acting like she’s not paying attention, her eyes closed. Caleb gasps for air, body still rocked with Veth’s orgasm, but his dick still so hard and so desperately in need of relief.

“Jester,” he begs. “Let her go.”

“What do I get if I do?” She asks, dark and tempestuous. Her eyes open just a crack and  _ gods  _ she terrifies him like this. Has she changed, or is this just what Jester looks like with a mantle of power about her?

“If you let her go, you get to see what she does.” He’s calm, he’s reasonable. He’s definitely not more aroused than he’s ever been in his life and he definitely isn’t afraid he might die if he can’t touch his dick in the next thirty seconds.

Jester looks at him, waiting to see his resolve crack, waiting to see through his mask. He has the most horrid sensation of prickling at the back of his neck, but it passes and she lazily smiles in his direction. There’s a sound he doesn’t want to contemplate as Jester retrieves her hand and delicately removes Veth from her lap, leaving her sprawled out in the tangle of her yellow dress. She stands, and walks towards him, calm and confident, pausing only so she can smear her still-wet hand across his face before walking off and leaving them to their own devices.

“Have fun!” She calls back, her laughter echoing unnaturally as she closes the door behind her, and leaves them trapped in his room, together.

They have a moment to themselves, breathing heavily, recovering, before Veth scrambles across the floor to get to Caleb and starts to work at untying him, steadfastly ignoring his entire pants situation. She’s mumbling apologies, trying in vain to get her dress to cover her, trying not to acknowledge what they both just went through. A part of him wants to let her, wants to pretend this never happened.

“Veth,” he says instead, and the fingers working to free his hands go still. “Get on my lap.”

She leaves him tied up, standing up to her full height to look him in the eye as if he’d just said the strangest thing anyone had ever said to her. He straightens in place as much as he can, meeting her gaze level and doing his best not to flinch. Still in disbelief, without a word, she climbs up on him, climbs until her dress drapes over both of them, propped up on her knees, still looking at him like he’d grown another head.

“Sit down,” he commands, and she does, the lips of her vulva still wet and brushing up against his dick. Her composure cracks just a bit as she gasps, her arousal still just as evident as his own. He gives an experimental thrust against her, and she responds in kind. A small game of chicken, they each make the smallest, most deniable moves, frustrating each other by inches, each hoping not to be the one that admits it’s really about time they were fucking.

“It’s really about time we were fucking,” Caleb says and Veth grinds herself on his dick, hard.

“You can’t want this,” she says in disbelief. “I’m doing this to you, somehow.”

“You are the most amazing woman I have ever met and I’ve wanted to make love to you for most of our acquaintance.” He’s calm, he’s matter of fact, he looks her in the eyes and lets that sink in.

“Even when I was-”

“Especially then.”

She makes an expression he can’t decipher then and buries her face in his shoulder, heaving sobs into him. He regrets not getting her to untie him.

“Yeza said you were looking at me like that, but I didn’t believe him.” She mumbles, her hips still thrusting against him in an easy, gentle rhythm. “He said- he said I should invite you in. Into our-”

“Veth, I would be happy to help your husband bone you senseless another time but just at the moment I am a little preoccupied.”

She laughs, wetly, and picks herself up from his shoulder, taking his face in her hands and kissing him, deeply, passionately. He kisses back as well as a man tied to a chair can. It’s both less and more romantic than he thought it ever could be. She lifts herself up even higher and one of her hands leaves his cheeks to go position his cock better to fuck herself on.

She holds him there, the tip of his cock just past her lips, one hand still on his cheek, a thumb brushing over the wetness Jester smeared there earlier. She licks herself off his face and he very much worries he might come just from that, his dick twitching so hard he almost falls out of her, but that’s the moment she moves, inch by torturous inch down onto him, giving herself time to adjust to the size of his cock in her each step of the way. It feels incredible, the warm sensation enveloping him, her eyes locked with his. He wants this. He wants every part of this.

She goes as far as she can down his length and holds there, savouring it. He’s hit with the lingering memories of what she imagined being full with him would feel like. He hopes he lives up to her expectations. He also considers some new things he might like to have done to him, things that he is now very much hoping she will help with.

“Caleb,” she says, her hand squeezing his cheek just before she plunges back in to mash her lips against his. He kisses back for all he’s worth, wishing he had a hand free to cup her ass, to tangle in her hair, to squeeze her breast, anything. She takes advantage of his predicament by moving her hand down to undo his shirt, reaching in and taking a nipple between thumb and forefinger, rolling them as casually as if they’d done this a thousand times before. She’s so tight around him, still waiting there, still getting used to him before she can really begin to move. It’s warm and comfortable, if a bit awkward, and the pressure around him has for the moment allayed his concerns of coming too early.

“I’m going to fuck you now,” she announces, giving him all the time in the world to object, but instead he just fixes her with a level gaze and a slight nod.

The first movements are soft and slight, he doesn’t even really move within her so much as she lifts them both up and down with a flex of her thighs. That soon changes as they begin to build a rhythm and work off one another, noises of all varieties filling this liminal space Jester has trapped them in. She moans his name and he pants hers, he gives her a awkwardly tender forehead kiss and she buries her face in his neck, biting him where Jester bit her, marking him so they’ll match.

They realise, eventually, that penetration isn’t going to be the thing that pushes them over the edge, and with a brief nod of acknowledgement from Caleb, Veth pulls herself off him, only to immediately grind back down, her hand trapped between them, clever fingers guiding him where she’ll enjoy him best.

“You know the really fucked up thing?” she laughs into his shoulder, one hand tangling in his hair. “We’re going to have to thank Jester for this.”

He groans at that, the last thought that pushes him over the edge and all too soon he can feel himself spilling against her. She takes that as her cue, her fingers abandoning his dick as she reaches for her clit and strokes herself to one last quick orgasm, crushing her body against his so he can feel every last shudder.

They stay there, for a moment, enjoying the afterglow, catching their breath. Savouring warmth that will very soon be leaving them.

“So,” Caleb asks, still tied to a chair, sticky in several places and with the woman of his dreams sitting in his lap. “Do we write her a card?”


End file.
